The Near West Side community in Chicago is home to two of the most famous culinary zones in city. In this area, you will find Little Italy and Greektown, providing you with a wealth of restaurants for you to sample along with the Maxwell Street Market. The entire area is fun to hang out in. Within the boundaries of the area are Malcolm X University, the Illinois Medical District, and Rush University Medical Center. Here, you will find a mix of single-family and multi-family dwellings with plenty of shady trees and sidewalks for you and your pup to explore.
As for the weather here, it is much like the rest of the Greater Chicago area. It can be bitterly cold with plenty of snow and wind. The summers here tend to be exceptionally hot with plenty of humidity, making early mornings the best time for the two of you to get out and start exploring.
Like most of the Greater Chicago area, Near West Side sits atop some of the flattest earth you are likely to ever see. The community is bisected by I-90 and I-290, but you are within an easy driving distance of Lake Michigan where you can find plenty of trails for the two of you to explore. Being immediately to the west of the City of Chicago, traffic here can make walking a bit challenging depending on what time of day it happens to be. The big thing, when faced with flat terrain, is finding a way to make your walks challenging. Since you don't have any hills or changes in terrain, the best thing you can do for yourself and your pooch is to take different routes every day, visit the different parks on a rotating basis, and even vary the times of day you go for a walk together.
Green space is not hard to find in the West Side area of Chicago. The biggest park in the community is the Addams/Medill Park. This park offers an athletic field, a soccer field, and acres of green space for you and your dog. In the northwest area of the community lie both Arrigo and Vernon Parks. Both of these parks offer acres of green space for the two of you to enjoy. Arrigo Park has a walking track that goes around the entire park and one that covers the center of the park.
Right next door is the smaller Vernon Park which is, more or less, a large green field with a few trees growing on it. Like most of the Greater Chicago area, you are only a short drive from the many dog-friendly parks and beaches that line Lake Michigan, so don't be afraid to get out and explore the surrounding areas.